An arylhydroxylamine compound is an extremely important compound as an intermediate such as, for example, polymerization inhibitors, antioxidants, agricultural chemicals, medicines, cosmetics and chemicals for an electronics industry.
As a method for producing an arylhydroxylamine compound, there are included, for example, (1) a method for subjecting a nitrobenzene and a hydrogen to a reaction, by using platinum-carbon (Pt/C) catalyst (see Patent Literature 1), (2) a method for reacting a nitrobenzene with hydrazine under reflux, in the presence of a platinum catalyst fixed on an ion exchange resin, (see to Patent Literature 2), and (3) a method for reacting a nitrobenzene with hydrogen gas, in the presence of a nitrogen base, a trivalent phosphorous compound and a hydrogenation catalyst (Pt/C) (see Patent Literature 3).
However, these methods have such problems that because of use of platinum-carbon, which is a combustible substance as a catalyst, sufficient caution is required in handling; progress of a reaction is delayed when hydrogen gas is used as a hydrogen source; because a reaction is performed under reflux, it is not preferable to be carried out in an industrial scale.
In addition, there is under investigation a method for producing an aniline in 100% conversion rate, by reacting a nitrobenzene with hydrogen gas, in the presence of a platinum carbonyl catalyst ([Pt12(CO)24]2−) (a hydrogenation catalyst) supported on quaternary ammonium group-introduced silica (see Non-Patent Literature 1). However, this method has a problem that a substrate is reduced completely to aniline without stopping at a stage of N-phenylhydroxylamine.
Under these circumstances, it has been desired to develop a method for producing an arylhydroxylamine compound efficiently and safely under mild conditions.    [Patent Literature 1] U.S. Pat. No. 3,694,509    [Patent Literature 2] WO2004/072019    [Patent Literature 3] WO99/28289    [Non-Patent Literature 1] Journal of Organometallic Chemistry 689, (2004), p. 309-316